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Product Details of [ 39515-51-0 ]

CAS No. :39515-51-0 MDL No. :MFCD00003353
Formula : C13H10O2 Boiling Point : -
Linear Structure Formula :- InChI Key :MRLGCTNJRREZHZ-UHFFFAOYSA-N
M.W : 198.22 Pubchem ID :38284
Synonyms :
m-Phenoxybenzaldehyde

Calculated chemistry of [ 39515-51-0 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 15
Num. arom. heavy atoms : 12
Fraction Csp3 : 0.0
Num. rotatable bonds : 3
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 58.35
TPSA : 26.3 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.11 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.23
Log Po/w (XLOGP3) : 3.38
Log Po/w (WLOGP) : 3.29
Log Po/w (MLOGP) : 2.61
Log Po/w (SILICOS-IT) : 3.22
Consensus Log Po/w : 2.95

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -3.59
Solubility : 0.0507 mg/ml ; 0.000256 mol/l
Class : Soluble
Log S (Ali) : -3.61
Solubility : 0.0486 mg/ml ; 0.000245 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.61
Solubility : 0.00489 mg/ml ; 0.0000247 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.55

Safety of [ 39515-51-0 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P301+P312-P302+P352-P304+P340-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 39515-51-0 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Upstream synthesis route of [ 39515-51-0 ]
  • Downstream synthetic route of [ 39515-51-0 ]

[ 39515-51-0 ] Synthesis Path-Upstream   1~10

  • 1
  • [ 39515-51-0 ]
  • [ 13826-35-2 ]
YieldReaction ConditionsOperation in experiment
99% With sodium tetrahydroborate In methanol at 0 - 20℃; for 1.5 h; 3-phenoxy-benzaldehyde (5 g, 25.22 mmol) was dissolved in dry methanol (60 mL), cooled to 0°C, and sodium borohydride (1.14 g, 30.26 mmol) was added portionwise. The reaction mixture was stirred at room temperature for 1.5 h and then concentrated under reduced pressure. The resulting residue was treated with saturated ammonium chloride solution, extracted with ethyl acetate, dried over anhydrous sodium sulphate, and concentrated under reduced pressure to provide the desired product (99percent, 5 g). LCMS: 183.0 (M+H), Rt. 5.4 min, 93.1percent (max).
99% With hydrogen In methanol at 20℃; for 4.3 h; General procedure: A mixture of 1a (196 mg, 1 mmol) and 1percentPd/Ni bimetallic catalyst9 (60 mg, 30 wt percent) in MeOH (10 mL) was stirred underH2 at room temperature and atmospheric pressure (on an atmosphericpressure hydrogenation apparatus) until the absorption of hydrogen ceased(3.5 h). After the catalyst was removed off by a magnetic stirring bar, thesolution was evaporated in a vaporator to give the product 2a
94% at 5 - 15℃; To a clean and dry round bottom flask SOOmL of methanol,lOOg of 3-phenoxybenzaldehyde (2)were charged and stirred for 15-20 minutes at 25-30°C. The mixture was cooled to 5-15°C and then 19.08 g of sodium borohydride was added lot wise over a period of 2-3hrs at 5-15°C. The reaction mass was stirred for 1-2hrs at 10-15°C. After completion of the reaction, the solvent is distilled off completely under vacuum and 200 mL of water was charged, then the reaction mass was stirred for 45-60 minutes at 25-30°C. The product is extracted with 3 x lOOmL oftoluene and the toluene solvent was distilled completely under vacuum. The obtained crude oil was degassed under vacuum at 65-75°C. Yield: 94percent.
Reference: [1] Patent: WO2015/130905, 2015, A1, . Location in patent: Paragraph 00209
[2] Tetrahedron Letters, 2015, vol. 56, # 46, p. 6460 - 6462
[3] Journal of Organic Chemistry, 2004, vol. 69, # 5, p. 1492 - 1496
[4] Patent: WO2018/42461, 2018, A1, . Location in patent: Page/Page column 7; 8
[5] Patent: US4366325, 1982, A,
[6] Synthetic Communications, 2002, vol. 32, # 2, p. 219 - 223
[7] Chemical Communications (Cambridge, United Kingdom), 2018, vol. 54, # 83, p. 11805 - 11808
[8] Synthetic Communications, 1989, vol. 19, # 7,8, p. 1217 - 1224
[9] Pesticide Science, 1998, vol. 54, # 1, p. 8 - 21
[10] Patent: US4304938, 1981, A,
[11] Bioorganic and Medicinal Chemistry, 2008, vol. 16, # 21, p. 9498 - 9510
[12] Chemical Communications, 2012, vol. 48, # 44, p. 5506 - 5508
[13] Journal of Medicinal Chemistry, 2016, vol. 59, # 8, p. 3750 - 3776
[14] Synthesis (Germany), 2016, vol. 48, # 23, p. 4143 - 4148
  • 2
  • [ 39515-51-0 ]
  • [ 3739-38-6 ]
  • [ 13826-35-2 ]
Reference: [1] Monatshefte fuer Chemie, 1936, vol. 67, p. 24,35
[2] Synthetic Communications, 1987, vol. 17, # 11, p. 1331 - 1338
  • 3
  • [ 3586-14-9 ]
  • [ 13826-35-2 ]
  • [ 39515-51-0 ]
Reference: [1] Australian Journal of Chemistry, 1989, vol. 42, # 8, p. 1351 - 1366
  • 4
  • [ 3586-14-9 ]
  • [ 3739-38-6 ]
  • [ 13826-35-2 ]
  • [ 39515-51-0 ]
Reference: [1] Australian Journal of Chemistry, 1989, vol. 42, # 8, p. 1367 - 1373
  • 5
  • [ 66230-04-4 ]
  • [ 1745-18-2 ]
  • [ 622-98-0 ]
  • [ 1875-88-3 ]
  • [ 2012-74-0 ]
  • [ 23853-78-3 ]
  • [ 3739-38-6 ]
  • [ 938-95-4 ]
  • [ 39515-51-0 ]
  • [ 873-76-7 ]
Reference: [1] Journal of the Brazilian Chemical Society, 2015, vol. 26, # 9, p. 1831 - 1837
  • 6
  • [ 39515-51-0 ]
  • [ 60677-14-7 ]
Reference: [1] Russian Journal of General Chemistry, 2014, vol. 84, # 11, p. 2264 - 2266[2] Zh. Obshch. Khim., 2014, vol. 84, # 11, p. 1906 - 1908,3
[3] Russian Journal of General Chemistry, 2014, vol. 84, # 11, p. 2264 - 2266[4] Zh. Obshch. Khim., 2014, vol. 84, # 11, p. 1906 - 1908,3
  • 7
  • [ 64-17-5 ]
  • [ 39515-51-0 ]
  • [ 60677-14-7 ]
Reference: [1] Bulletin of the Korean Chemical Society, 2011, vol. 32, # 6, p. 2070 - 2072
  • 8
  • [ 124-63-0 ]
  • [ 39515-51-0 ]
  • [ 102851-06-9 ]
YieldReaction ConditionsOperation in experiment
92.1% With dmap; aqueous KOH In 1-methyl-pyrrolidin-2-one; hexane; water; toluene EXAMPLE 3
A mixture of 4-(dimethylamino)pyridine (0.50 g, 0.0041 mol), sodium cyanide (13.50 g, 0.275 mol), 3-phenoxybenzaldehyde (51.05 g, 0.250 mol), (R)-2-(2-chloro-4-trifluoromethylanilino)-3-methylbutanoic acid (71.58 g, 0.242 mol) in N-methylpyrrolidinone and "mixed" picolines (obtained from Reilly Tar and Chemical Co.) (42.5 g, 0.455 mol) is heated with stirring to 55° for 2.5 hours.
The reaction mixture is then cooled to 20° and hexane (100 ml) is added.
Methanesulfonyl chloride (33.49 g, 0.293 mol) is added slowly over 1.75 hours while maintaining an internal reaction temperature of 15°-20°.
After 2 hours at 20°, additional methanesulfonyl chloride (0.50 g, 0.004 mol) is added and the mixture is stirred for 1 hour.
Then water (2.50 g) is added, followed 1 hour later by addition of hexane/toluene (80/20; 330 ml) and water (200 ml).
The phases are separated and the organic phase is washed with water, with 10percent aqueous HCl solution, with water, with 5percent aqueous KOH solution, and with three portions of water.
The solvent is stripped off to give (R,S)-α-cyano-3-phenoxybenzyl (R)-2-(2-chloro-4-trifluoromethylanilino)-3-methylbutanoate as an amber colored oil.
Yield is 92.1percent (based on the weight of the starting butanoic acid).
Reference: [1] Patent: US4849536, 1989, A,
  • 9
  • [ 2393-17-1 ]
  • [ 39515-51-0 ]
  • [ 885101-89-3 ]
YieldReaction ConditionsOperation in experiment
86%
Stage #1: at 100℃; for 0.166667 h; microwave irradiation
Stage #2: With sodium tris(acetoxy)borohydride In 1,2-dichloro-ethane at 20℃; for 1 h;
Stage #3: With water In 1,2-dichloro-ethane
Compound XV, 3-(4-(3-phenoxy-benzylamino)phenyl) propionic acid. Representative procedure where n = 1 , Z = H, X = NH and Y = 3-C6H5-0-C6H5 [00115] To a solution of 3-phenoxybenzaldehyde (3.2 mL, 18.5 mmol) in dichloroethane (60 mL) was added 3-(4-aminophenyl)propionic acid (3.0 g, 18.5 mmol). The mixture was sonicated and transferred in a microwave vial (20 mL). The reaction was irradiated at 100°C for 10 min in the microwave. The solution was transferred to a 500 mL round bottom flask and sodium triacetoxy borohydride (7.8 g, 36.9 mmol) was added in a small portion to the mixture. The reaction was stirred at room temperature for 1 h. To the resulting slurry was added water (100 mL) and the organic layer was separated. The latter was extracted twice with water (100 mL) and dried over sodium sulfate. Solvent was then removed and the crude product purified by column chromatography on silica gel using hexanes:ethylacetate (1 :1 ) with trace acetic acid. This gave pure 3-(4-(3-phenoxy-benzylamino)phenyl) propionic acid (5.5 g, 86percent) as a low melting point solid. 1H NMR (CDCI3) δ 2.40 (t, 2H); 2.63 (t, 2H); 4.21 (s, 2H); 6.09 (bs, 1 H); 6.44-6.47 (m, 2H); 6.81 -6.83 (m, 1 H); 6.87-6.89 (m, 2H); 6.94-6.97 (m, 2H); 7.07 (bs, 1 H); 7.1 1 -7.18 (m, 2H); 7.29-7.33 (m, 1 H); 7.35-7.38 (m, 2H); 12.09 (bs, 1 H); MS m/z = 348 (M+H+).
Reference: [1] Patent: WO2012/97427, 2012, A1, . Location in patent: Page/Page column 41-42
[2] Journal of Medicinal Chemistry, 2007, vol. 50, # 13, p. 2981 - 2989
[3] Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 7, p. 1840 - 1845
  • 10
  • [ 16642-79-8 ]
  • [ 39515-51-0 ]
  • [ 885101-89-3 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 6, p. 1584 - 1589
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